5848-28-2

Upstream product

• 592-82-5 butyl isothiocyanate 
• 109-73-9 N-butylamine 
• 10191-60-3 dimethyl N-cyanodithioiminocarbonate 

Downstream Products

• 41283-66-3 N-cyano-N’-butylguanidine 
• 60178-41-8 1-butyl-2-methyl-3-(3-phenyl-[1,2,4]oxadiazol-5-yl)-isothiourea 
• 59566-69-7 1-butyl-2-methyl-3-(4-oxo-6-phenyl-4H-[1,3,5]thiadiazin-2-yl)-isothiourea 
• 60178-45-2 1-butyl-3-[3-(4-chloro-phenyl)-[1,2,4]oxadiazol-5-yl]-2-methyl-isothiourea 

Relevant academic research and scientific papers

Syntheses and Crystal Structures of Methyl N-Substituted-N′-Cyanocarbamimidothioates Derived from Dimethyl N-Cyanodithioiminocarbonate

Abstract: Reaction of dimethyl N-cyanodithioiminocarbonate and arylamine or alkylamine compounds in the refluxing ethanol solution afforded the according methyl N-substituted-N′-cyanocarbamimidothioates 1–16 in good yields. Compounds 1–16 were characterized by proton nuclear magnetic resonance (1H NMR) and infrared spectroscopies, of which the structures of compounds 1, 2 and 3 (Elgemeie et al. in Acta Cryst E71:104–111, 2015) were established by X-ray crystallography, showing that weak hydrogen-bonding interactions exist in compounds 1–3. Compound 1 crystallizes in the orthorhombic space group Pbca, with a = 6.997(2), b = 7.395(2), c = 36.112(11) ?, and Z = 8. The unit cell of 2 has a monoclinic P21/c symmetry with the cell parameters a = 5.8717(12), b = 4.6598(9), c = 37.799(9) ?, β = 91.126(6)°, and Z = 4. Compound 3 crystallizes in the orthorhombic space group Pbca, with a = 7.123(3), b = 7.374(3), c = 38.538(16) ?, and Z = 8. Graphic Abstract: A series of methyl N-subsituted-N′-cyanocarbamimidothioate compounds were efficiently synthesized via the reaction of arylamine or alkylamine compounds with dimethyl N-cyanodithioiminocarbonate. The structures of compounds 1–3 were characterized by X-Ray crystallography.[Figure not available: see fulltext.]

Regioselective preparation of N-substituted 3,5-diamino-1,2,4-oxadiazoles

Regioselective preparation of 3,5-diamino-1,2,4-oxadiazoles which have a substituent on one or the other amino group has been developed. When 1-substituted 3-cyano-2-ethylisourea (2) was allowed to react with hydroxylamine under basic conditions, 5-amino-3-(substituted amino)-1,2,4-oxadiazole (3) was obtained in good yield. On the other hand, 3-amino-5-(substituted amino)-1,2,4-oxadiazoles (4), a regioisomer of 3, could be synthesized by the reaction of N,O-bis(trimethylsilyl)hydroxylamine (9) with 2 or 1-substituted 3-cyano-2-methylisothiourea (1) and subsequent alcoholysis.

Synthesis and biological evaluation of sulfonylcyanoguanidines and sulfonamidonitroethylenes as bioisosteres of hypoglycemic sulfonylureas

Sulfonylcyanoguanidines and sulfonamidonitroethylenes are bioisosteres of hypoglycemic sulfonylureas and were prepared and evaluated for their insulin release potency from rat pancreatic islets. At 25 μM, both bioisosteres of glibenclamide, sulfonylcyanoguanidine 22 and sulfonamidonitroethylene 23, were as patent as their parent on insulin secretion.